Hydrochloric Acid → HCID 71665914, compound

HRID 929064Notes

Reaction equation

HRID 929064 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([NH:13][O:14][CH2:15][CH2:16][O:17]C=C)=[O:12])[C:3]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[Cl:28].Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([NH:13][O:14][CH2:15][CH2:16][OH:17])=[O:12])[C:3]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[Cl:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 89704812HCID 89704812, compound

Product 1

HCID 71665914HCID 71665914, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 4-fluoro-5-((4-bromo-2-chlorophenyl)amino)-N-(2-(vinyloxy)ethoxy)benzo[d][1,2,3]thiadiazole-6-carboxamide (191 mg, 0.39 mmol) in CH2Cl2 (10 mL) was added 1.0 N HCl (aq., 1.5 mL, 1.5 mmol). After stirring for 1 h, the reaction mixture was neutralized with saturated NaHCO3 (aq.). The aqueous layer was washed with CH2Cl2 (10 mL×2). The combined organic layer was washed with water (30 mL×2) and brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 20:1, v/v) and gave the desired product as a yellow solid (150 mg, 66.5% yield for two steps). 1H NMR (400 MHz, CD3OD): δ 8.53 (s, 1H), 7.69 (s, 1H), 7.34 (d, 1H), 6.74 (m, 1H), 3.91 (m, 2H), 3.62 (m, 2H). MS APCI (+) m/z: 462.5 [M+H].

Workup

  1. washThe aqueous layer was washed with CH2Cl2 (10 mL×2)
  2. washThe combined organic layer was washed with water (30 mL×2) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 20:1

Sources & evidence

ORD record
ord-5c9cda521cb24bbc8374c3f574c238be
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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